The Headmaster – Chapter 1

Brigitte Durning almost clipped her FBI badge onto her belt as she would normally have done on any other work day. However, this day she was to start as new History teacher – Anna Sharpe – in her first major undercover case. Brigitte new, of course, that she would never ever live it down if she blew her own cover on the first day by wearing her badge right out there for everyone to see.

She looked into her bathroom mirror and saw that her dark red hair was sufficiently un-sexied by having it pulled back and into a scrunchy that made her look much more reserved than she ever would on her own. Brigitte then focused on her eyes. No, the make up wasn’t “too much”, but she did try to soften the expression in them. Her brown eyes were expressive and confident and knowing. She really wanted to appear to be a little less knowing and less confident than she should be.


Sandra Matthews knew one thing for certain: she would be severely caned for the incident. Against school policy, the law, and any degree of common sense, she had decided to make a small business within Blenham Academy of selling off stolen prescription pills from her mother’s house. It was easy enough to get caught. All it took was for one envious cheerleader to decide to make a power play of being a tell-tale and Sandra found herself facing the headmaster.

The headmaster – Dr. David Pendrake III – peered, frowning at the report he had just read as if he couldn’t believe his eyes. He looked up at Sandra standing before him and looked back down at the paper.

Sandra thought, ‘If I didn’t know better. I’d swear he was enjoying stretching out this time before announcing my punishment. If I didn’t know better… ”


Jessica, Pima, and Rosalyn, Sandra’s friends, stood outside the door to the headmaster’s office. They began speculating about what was happening to her.

Jessica said, “If it is drugs, he’s probably going to say that he can just call the police or not involve him and give her a caning.”

“A caning,” Pima said, instinctively reaching behind her with one hand, rubbing her bottom and looking rueful. “A small word for a lot of pain. I got 3 dozen strokes once.”

Rosalyn answered, “I got 50 once myself and then got a strapping when I got home.”

Jessica said, “You know they say that there’s a vent in the teacher’s lounge bathroom where you can hear what’s happening in his office quite clearly.”

The three looked at each other for a moment, considering the idea. Jessica nodded her head sideways indicating the direction they should go. She lead the way and the others followed.


Dr. Pendrake, after giving the situation some thought, said, “You’ll need to be caned of course.”

Sandra swallowed har and her eyes widened and seemed to look far away. “Of course,” she repeated mindlessly, shaking her head slightly.

“Sixty strokes then,” Dr. Pendrake said. “Bend over my desk and grab the far side.”

Sandra walked over to the desk. The place where the desk met her hips was a bit high and she had to come up on her toes a bit to bend over the desk. As she did so, and her center of gravity shifted forward, her torso rested on the hard wood. She stretched across the blotter and grabbed the other side.

Dr. Pendrake walked around behind the desk to a glass door cabinet lined with 7 canes. He looked at the bending girl’s skirt-clad bottom and back at the canes. Sandra could see this whole interaction of course. He selected one that was not the thickest, but did have considerable density. He swished it through the air and it made almost a low-pitched “whoosh” sound. The whoosh was so low and heavy, it automatically inspired fear in Sandra.

He walked back around to stand behind Sandra and to her left. He swished it through the air once more.

“Face me, Sandra,” he said, “I have to monitor your face so that I can make sure you’re alright…. medically.”

She turned her face to his direction. From the angle he was standing he could see both her face and see her buttocks and hips well enough to make a good stroke. He took aim and gave Sandra her first biting sting of a cane stroke.

“Yeowch,” she yelped.

Even though she was being caned over her skirt, each stroke still hurt enough to be a punishment in itself. The thought that she would take 60 strokes altogether was a bit overwhelming and she began to panic and become breathless.

“Do try to relax, Ms. Matthews,” Dr. Pendrake said, “You can deal with this. One stroke at a time.”

He gave her another stroke and she yelped again. He did it a third and a fourth time, establishing a rhythm…


Whoosh, whap, “yeowch” was heard repeated at a regular three or four second intervals as Jessica, Pima, and Rosalyn listened from that secret vent in the teacher’s lounge bathroom. They knew they had limited time in there because soon the current class hour would be ending and some teachers would be coming into the lounge for their break time. Yet they had become almost entranced listening to Sandra’s caning, having not heard the beginning of it, could not be sure how long it had been happening. So they had no idea how much longer it would go on. They felt sorry for her, realizing how much pain she must be in, her bottom likely bruised by now and tears streaming down her flushed cheeks.

“Wow,” Rosalyn commented. “I hope she doesn’t have to go through another spanking at home like I did.”

“I hope so too,” Jessica said, “But we’ve got to get out of here. We don’t want to get caught.”

Jessica peeked out from the bathroom door, and seeing no one there, stepped out, motioning the other two out as well. Just as they reached the exit door of the lounge two teachers were walking in. Teachers were surprised to see students and students surprised to see teachers.


In fact tears were streaming down Sandra’s flushed face. She gripped the other side of the headmaster’s desk as strongly as if she were hanging from a cliff.

Dr. Pendrake pulled her skirt up and draped it over her back.

“You’ll get these final dozen over your panties,” he said.

Sandra pleaded, crying, “No no no no… please! I promise I won’t do it again!”

“I believe you Sandra,” Dr. Pendrake said, smiling slightly. “I believe in my heart you’re a good girl, really.”

He continued on with caning her over her panties. She wanted desperately for the caning to be over or to pass out, whichever favor the universe might grant her.

She was finally granted the former. Her sixty-cane-stroke punishment was finally over.

Sandra was allowed to stand and as soon as she did her hands flew behind her so she could rub her bottom and dance about with the terrible stinging ache. It felt to her almost like she were still being caned, which of course was unacceptable.

As she rubbed her bottom and composed herself, Dr. Pendrake dialed Sandra’s mother.

“Yes,” he said over the phone. “This is Dr. Pendrake – headmaster at Blenham Academy. Yes. Yes, I’m afraid I’ve had to cane Sandra. Yes, sixty strokes…”

He further explained that the caning did complete her punishment and that there was no need for suspension or calling the police. But Sandra knew that would certainly not be the end of her punishment. Since she’d been caned at school, she could look forward to having a very long over-the-knee spanking at home. Strapping wasn’t necessary. Each spank of  a hand on her freshly bruised bottom would be as punishing as the cane strokes. And she knew she’d have to endure at least 200 spanks.


Brigitte Durning, in the form of teacher, Anna Sharpe, after being shown her teaching room and her office, was now waiting to meet with Dr. Pendrake. While she waited, she could have sworn she heard the sound of someone saying “yeowch” over and over….